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Publication numberUS892897 A
Publication typeGrant
Publication dateJul 7, 1908
Filing dateMar 13, 1908
Priority dateMar 13, 1908
Publication numberUS 892897 A, US 892897A, US-A-892897, US892897 A, US892897A
InventorsKarl Schirmacher, Hermann Landers
Original AssigneeHoechst Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Red vat dye.
US 892897 A
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Description  (OCR text may contain errors)



lltltllS'F-OX-(Flll'Z-MAlN, GERMANY, it Bltb'NlNG, or riorusr-rm rnn- MAIN, GERMANY, A CORPORATION OF GERMANY.


Specification of Letters Patent.

'Patented July 7, 1908.

Application filed March 13, 1908. Serial No. 420,863.

T 0 all whom it may concern:

Be it known that we, KARL Sonnmmonnn, l

Ph. D., and HERMA'NN Liinnnns, Ph. 'D.,

chemists, citizcns of the Em pi r0 of Gernurny,

and residing at ll6chst-on-the-Moin, Gernnmv, have invented certain Improvements winch the are red coloring nuitters,

shades and their fastnoss.

halogen phony]thioglycollic boxyhc itcld of the constitution 3 (CH :Hlg:SOH. C0011 :COOll 3:5:1 :2)

with alkalies and treating the methidhulomeans of acetic acid. The acid genoxythionaphthene-carboxylic thus obtained with oxydizing agents.

The process may be carried out, for instance, as follows: 21.6 parts by weight of the chloronitrotoluylic acid- (CH5:C.l:COOH,NO=325z2z1) (see Liebigs Anna/la cle'r' Chem/i0 274 p. 298) are dissolved in 5.6 parts by wci ht of soda and the necessary quantity 0% water, a concentrated solution of 11 parts by weight of sodium disulfid (Na.,S.,) is added and the mixture is boiled on a reflux cooling apparatus. When cold, the mass is ocidi fied with acetic acid and the precipitated chloroamino-orthotoluylic acid (CH :Cl:COOH: NH =3:5:2:l) is filtered. In orderto purify, it may be dissolved with soda and reprecipitoted by crystallizes from water, in which it is soluble with some difficulty, .in form of fine needles. 17.6 parts by weight of this rn-chloro-ni-eminoo-toluyhc acid are diezotized with 25 parts by weight ,of hydrochloric acid and 6.9

hitherto unknown. j

the dyoings of. which are distinguished by their beimtiful .lhese new d veortho our 1 parts by weight of nitrite, and this (llttZU solution is introduced into a solution (if-1S parts by weight of potassium Xonthogcnute and 40 parts by "weight of soda. After several hours stirring 15 parts by weight of sodium chloroocctrrtc and 25 parts weight ofcnustic sods Ive of 40 B6. strength are added and the solution hearted for some hours'to 100 C. At the surface ol" the so lution small qrumtitics of o violet blue dyestuil separate, which turn to red when acidified. 'hcn cold, the solution isiiltored and then the unmet]ryl-m-chlorophenyland common salt. The acid separating as s week mass soon becomes solid. 1t may be recrystallized. from water and thus ohtuined in the form of fine nearly colorless needles.

To produce the iii-mothyl-m-chioro-oxythionuphthene-cm'boxylic ncid,.20 parts by weight of metliyl-chloro-phenvlthioglycollico-eurboxylic acid are heated to'ubout 180- 190 (lwith a mixture of 100 parts by weight of caustic soda and 10 parts by weight of wnter. The melt, at first intensively colored, becomes successively clearer and finn'r v very light-vellow. When cold, the melt dissolved in water; then bv adding to the cold solution hydrochloric acid the methyl-chlorooxythions lithene-corboxylic acid 13 precipitated in t e form of white flakes which become a reddish color l l l i thioglycollic orthcrcurboxylic acid is l splits oli' darhonic acid and the methyl-chloro-o:-;ythionephthene is formed which is very dillicultl Y soluble in water and forms when recrystal ized from water fine brilliant needles.

In order to obtain the vet dyestutl" from boxylic acid, the alkali melt may be used d1- rect-ly by dissolving it with water and sddin :1 solution of potassium fcrricyanid unti. there is an excess of it. The new dyestuif separates in beautiful red flakes. In a dry state it is a red powder which dissolves in an alkaline hydrosulfite solution thus forminge l vet.

adding hydrochloric :Mlltl when exposed to theair. If this acid be heated with mineral acids it the methyLL-hloro-oxythionaphtliene cer- Tln's dye vat dyes wool and cotton in thioindigo, the constitution of which correfast alizarin pink shades. The dyestufl' is sponds to the formula:

I not soluble in water, ether and alcohol, soluble with a red color in hot glacial aceticncid, s nitrobenzene, anilin and c loroform, with a l /\/LO' /w\/\ green color in concentrated sulfuric acid;

Having now described our invention, what cl/\/\ 5 S I We la m i l l it is a, red powder, insoluble in alcohol, ether.

As new P the yl-dlh'aloand water, soluble in hot nltrobenzene, gla- 3? gen derivatives of thioindigo, the c0nstituj cial acetic. acid and chloroform with a red 10 tion o hi h orresponds t th fo m a: color, in concentrated sulfuric acid with a CH 00 CO on, green color, dissolved with alkaline hydro- I sulnte it forms a yellow colored vat dyeing lilgl l lH g I wool and cotton in beautiful fast alizarin- S S pink shades.

15 red powders, insoluble in water, alcohol and In testimony, that we claim the foregoing ether, soluble in hot nitrobenzene and glacial I as our invention, have signed our names In acetic acid with a-red color, 111 sulfuric acid J presence of two SUbSGIlbIII witnesses.

with a green'color; when dissolved with al- 5 ,KARL SCHIRMACHER. kaline hydrosulfite, they form a yellow col- 1 HERMANN LAN DEBS. :20 ored vat, which dyes wool and cotton in fast Witnesses:

pink shades. i J EAR GRUND,

2. As a new product the dimethyl-dichlor- CARL GRUND.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US6864210Feb 6, 2003Mar 8, 2005Equistar Chemicals, LpBimetallic olefin polymerization catalysts containing indigoid ligands
Cooperative ClassificationC09B7/10